1,5-Dihydroxynaphthalene → HCID 86724457, compound

Participants

Reaction Steps

Into a 1,000 ml two-necked flask equipped with a refluxing condenser, 20.0 g of 1,5-dihydroxynaphthalene (Sigma-Aldrich), 51.81 g of K2CO3, and 500 ml of acetone were charged and mixed at room temperature. Then, the reaction temperature was set to 80° C., and homogeneous mixture was refluxed (hereinafter, the temperature written during the synthesis represents the set temperature of the refluxing apparatus and was higher than about 10° C. to 15° C. than true reaction temperature of reaction medium). During the refluxing, 13.5 ml of allyl bromide (Sigma-Aldrich) was added in a dropwise manner and allowed to react overnight. After finishing the reaction, the reaction mixture was cooled to room temperature and was filtered using Celite. The solvent was evaporated to obtain a coarse product. A reaction product was extracted from the coarse product using ethyl acetate, washed three times using water, and dried using MgSO4. MgSO4 was filtered off, and solvents were removed by using an evaporator to obtain an intermediate product (11), 5-(allyloxy)naphthalene-1-ol. The reaction scheme in the 1st step and the NMR data of the intermediate product (11) thus obtained are as follows.

Provenance & Evidence